[upbeat music] Hey friend, it's David Nebinsky, the community lead here at the Chief of Staff Network.
We help chief of staff through the three Cs: cohorts, curriculum and community via Slack with over 900 people in it. Learn more about membership, events and courses at chiefofstaff.network.
There you'll see our upcoming Chief of Staff Connect conferences in New York in October and London in November. And so in this episode we talk about leveling up. Are you looking to level up as a chief of staff?
Well, this episode was recorded during a podcast and dinner event in New York City. Special thanks to our friends at JLL for hosting us.
In this episode, you'll hear from more than six chiefs of staff who discuss ways on how they have been leveling up: stories, experiences, thoughts on this topic.
After you listen to us, definitely check out our leveling framework on our website at chiefofstaff.network. So excited for you to level up as a chief of staff. Here we go with people sharing stories.
Welcome to the Chief of Staff podcast. We're h- here in JLL's boardroom. Not... Unofficial boardroom. Um, but yeah, thanks Haley and Doug, uh, JLL, for having us here, uh, in New York. Okay.
So the topic of leveling up as a chief of staff. Um, one thing that came to mind for me as I was thinking about this was something in 2019 when I was working with someone as a chief of staff, um, there was like just some
almost like unspoken miscommunication around, like, what was getting done or not, or what was priority or not.
And I then decided to, very basic, uh, but just create a Google Doc and just share, like, what are the priorities and, like, what are the tasks and just, like, have them listed.
And then I was like, "Here's what I'm working on today."
And then this person would then just, like, comment and be like, "No, you don't need to work on that," or, "You don't need to work on this," or, "I'm gonna take care of that."
But just this simple Word document of just, like, what are the tasks and activities, um, that we both could look at and both could see, was like a game changer for, like, productivity.
Um, and also it just helped me be more confident in the stuff that I was doing and not be, like, concerned, like, is this... Like, is this just a story I'm telling myself of what I should be doing?
Um, so yeah, just a very simple low-tech approach, like, really, um, help us achieve a lot more, but also, like, mentally it was a lot better for me, um, 'cause we were remote at the time and, um, yeah.
So s- big tech is, is good, but low tech like Google Docs can also be really helpful too. So, uh, yeah, anybody have, uh, any s- uh, follow-up questions to this little story of mine? I can add on. Yeah.
In the theme of- Yeah... moving to low tech, um,
when you were telling me that story, I was thinking about a similar situation where we were using a system, Lattice, I think you guys are familiar with it, for performance tracking.
And we were trying to push OKRs and making it complete in the system, and it was becoming aware-- I was becoming very aware that this was becoming more of an administrative task.
And to your point, like, well, first principles thinking, like, what are we actually trying to do here? Yeah. Not trying to create more work and tasks that don't need to be entered into a system.
And I also did the low-tech approach too on Google Sheets.
It's collaborative, it's easy visibility, there's no training of employees to have to know how to use it, and same thing, moved a lot of the goals and was able to trim down a new system to simplify it,
and it worked out better in terms of visibility. And, you know, Lattice is still a system we used for engagement surveys and results. It wasn't just we bought it for this, the goals.
So yeah, being able to rethink, you know, is this my doing tech to add tech to it, or is it actually, like, making it efficient?
Which is, I think, the whole conversation around AI, which I'm sure one of us will get into later- [laughs]... on, you know, what are we using AI for? Um, is there actually, um... Did we think through this?
So that's my story.
Similar to you, Jill, uh, we were implementing a shipping bonus program, so meaning, like, different teams had different budgets for their head count to give shipping bonuses at the end of a quarter, certain dollar amounts for certain roles.
Not necessarily complex- Mm-hmm...
but still needed to be tracked and easily findable and usable for the team, and it was a new thing we were spinning up, and what's the budget, and how often do people use it, and how do we track it?
And we were thinking a whole bunch of things. Should we buy a new platform for it? Should we buy some kind of money something or other?
I don't even remember what we looked at, but at the end of the day we said, "Well, if it's tied to work being shipped, why don't we just build it within our sprint planning mechanism?" Which was monday.com at the time.
And I figured, how could you put a shipping bonus program in a task management tracker? But it ended up working out.
We combined boards so that managers could see what people shipped, if it was worthy of a shipping bonus, if it really mattered how many story points, you know, across different things.
And then in Monday, it was a tool they were already using and comfortable with, so it was so easy, and we actually got so much adoption for a program that actually meant a lot of people to our team because it was a low barrier to entry.
So I completely agree on the low tech aspect. And then of course, as you mentioned with AI, you know, the barrier to entry is even lower, but it's meeting the team where they are with the tools they already have.
Any follow-up questions to either of us? Lauren, what was, um, what was it like in conversations with the team about this? It was quite easy, actually.
Like, a lot easier than I expected because thankfully, we had a culture within our team of wanting to give praise always.
And-There are definitely people that when they're praised, they like that there's, you know, dollar amounts attached to it. Like, there are people that are very motivated by that.
So it was a tool they were already using, and it was a tangible way that they can continue to keep certain people on their teams motivated.
And in truth, it was for a lot of our engineering teams and product teams and analytics teams, and, you know, they are more motivated by that.
So they were thankful we created the budget, and so they were more willing to use it because we met them where they were, and then we didn't put them into another system that they had to remember to do. We had reminders.
We had automations. It was just so easy for them to remember to do something that meant a lot to their teams, and then especially leaders became better leaders because they were recognizing work more.
So it really just became this, like, very well-rounded relationship around this tool and program of people feeling really valued for what they did.
You touched upon this a little bit, but can you go into how you introduced it to the team? Like, what was the communication like, and then how did you help embed some of that behavior? Such a good question.
So we had, we have weekly all hands where every week we go through different departments, different updates.
You know, uh, I have a section where we do shout-outs and administrative updates or sort of like HR people updates.
And what we did is we said that would be the, the big announcement of what we're trying to do and what the purpose was and how it related to our values and sort of what the system would be.
But then before then, we shopped it around with the different team leads to say, "This is something that we wanna do. We wanna make sure that you have a way to, without asking for permission, reward your team.
So you have a budget per quarter per head, and if you wanna use it, you don't have to ask us. So you have the autonomy to reward your team."
So we went to them first to basically give them the power and autonomy to be a leader and reward their team when it made sense without having to ask for approvals.
And then once we had their buy-in, we announced it to the whole company and then followed up with questions.
So it was very simple, but we basically started with the leads, empowered them, and then essentially went to the whole team and said, "This is something that we wanna do.
We wanna have a much more robust rewards program." We-- n- rather than call it shipping bonus, we called it a rewards program, and then we lumped in, you know, a couple of other things over time.
Sometimes it was swag, sometimes it was, you know, a, a, a paid long weekend, right?
Like, it, it evolved over time, but it started as just a simple rewards program to, you know, reward shipped work when things got really tough, and then, you know, different things came about from there.
And then we kept announcing it at this... This, this weekly all hands was, like, the-- our core of how we got announcements across the team. Gonna take a turn on your question, but similar.
Um, you've mentioned culture, rewards, recognition a lot of times during these different follow-up questions.
What role did you play in that as a chief of staff, and do you feel like that was something that made you, you know, differentiated yourself in the role? These are such good questions.
I'm overwhelmed by how good these questions are. Um, so I started out in HR. That's my background.
So people, culture, rewards, benefits, that's how I-- I always say that's how I grew up in my corporate career, and I majored in psychology.
Uh, and then from there, I evolved into a chief of staff because I joined a small company, and you just had to do a lot of things. Um, so
I would say it differentiated me because chiefs of staff usually grow up from, like, a consulting background or an MBA, which is great and very necessary for the role, but they come with a much more business-focused and strategic mindset, rather than sort of the people first.
And they usually learn that side of it. So I would say
because I started out on the people culture reward side and that was sort of my specialty, it made implementing the chief of staff role in my small business at the time not as bureaucratic because I was close to the people and I was still running the people.
I wasn't just coming in to be the voice of a CEO, and then they lost access to our founder because they had to go through me first. Like, sometimes if you don't...
It's like change management can feel very bureaucratic if not done well.
So I think because I started out with managing the people first as a true HR person and then just transitioned into other capabilities, I still kept HR, which kept me differentiated.
So culture and rewards and psychological safety is critical to me for success. Um, does anybody have a story related to leveling up in terms of getting more resources or different scope of work or, um... Yeah.
Or another story. That's fine too. [laughs] Um, a short story, hopefully. Uh, uh, yeah, getting more resources and on the topic of leveling up with tech or leveling down.
This is a leveling up, um, story, I guess. Um, I was working with a researcher in residence at a venture capital firm in San Francisco, and, um, he only had about...
So I guess this is, like, more of a fractional chief of staff role. Um, we, we spent close to, like, six months working on a campaign rollout, but our budget was slim,
and part of it was, um, hosting a gallery exhibition on third spaces. So, like, wellness spaces and just, like, looking at that, um, that industry and how it's about to boom and is booming.
Um, and we wanted to document that. So we did it both, like,
in the form of an art gallery that was open to the public, but then also a VIP dinner gathering, hosting San Francisco Bay Area founders, CEOs, people that have built third spaces and are running them successfully.
But we were tight on budget. We had to cover a dinner and then also produce a gallery in about six weeks, which was absurdAnd so, um, one of our...
I guess you could say we-- So leveling up in that capacity was, like, sourcing artists. Suddenly I'm, like, in San Francisco.
I'm like, "Who do I know that's an artist that wants [chuckles] to be showcased, like, in a few weeks?"
Um, and one of my, um, connections actually was very interested in getting to know Runway, which is, um, an AI platform for producing multimedia, but mostly video.
And he was able to basically within a week create, like, a three-minute fully polished piece that, like, took our entire brand narrative in terms of what we were trying to convey about Third Spaces just by p-prompting, um, Runway to generate images or, like, just feeding Runway images or, like, small tracks.
Um, and then suddenly we had, like, a five-minute piece, and it was up in a gallery. Wow. So that, that's one example. Another example would be probably using Midjourney. I don't know if anybody's been using Midjourney.
But, like, when you're at a stage where it's like, you know, something's coming into form but the brand is not, like, so clear yet, the design is not so, like, refined, and you can't...
you don't have the resources to hire a designer just yet but you kinda need an image in order to pull traction, um, Midjourney has been amazing for, um, yeah, generating images that don't feel like stock photos.
It's like, again, you can prompt it to pull in the aesthetic, the tone, the... I don't know. I really, I really enjoyed using that, and I found it very helpful for buy-in and for, uh, attendance. So that's my story.
So this will be a more generic chief of staff leveling up. I feel like I have to speak. If I was chief of staff for three years, I hope I leveled up during that time. [laughs] Like, at least once every year, right?
Um, so I tried to break it down by year.
But I think because of that journey, I speak to it as the way I leveled up, it's hard to measure because I think the true result was being able to have strong relationships, and that's where, Lauren, I
keyed into your culture and people background because I luckily had a, an experience. I mean, it was the pandemic when I was...
my first year of chief of staff, coupled by the chief people officer had joined a month or two.
So we were a team both from, like, an executive presence standpoint and engagement surveys and knowing that we were sort of the softer skills of the organization. But, um,
what I was getting at is I think I really took a lot from that experience of learning the softer skills of how do I communicate the CEO, who's sort of aggressive, towards his priorities in a way that works well with the people.
And I measure that for the depth of the relationships of if I had to ask a favor of someone that was a VP, they would listen to me or they are on a text basis with me or, you know, I established strong relationships in that mid-management layer, and that's really the key unlock to getting stuff done.
I was at a company size 300. And I didn't strategically go about it in that way.
I knew I had to work with many departments, um, so ult-ultimately that was my success, um, knowing I felt if I had to collaborate with a depart-a department, they knew I was coming from both a place of authority but also a people first place.
Yeah, I guess this kind of follows theme. Um, when
I, you know, first joined the company I'm actually at now, um, I was actually a consultant that became, uh, full-time and, you know, there was pretty quickly in, they needed me for, like, more and more hours, and I really had to, like, step in and kind of like fill the gaps as most a lot of chief of staffs have done.
And kind of following theme with kind of rolling into the people kind of org, um, you know, our, um, head of people at the time had left, and there was, like, this gap there, and I was like, "Well, done this enough to...
Like, I've been an interim, like, people person enough to kind of, like, fill it." Where I feel like a lot of it is just being brave enough to be like, "Okay, I do know how to do this. I've done it in the past.
Like, my previous work has translated into this," and just kind of, like, rolling into it.
So I was like, "Oh, I'll be, like, interim head of people on top of being chief of staff on top of being ops" and, um, you know, rolling with everything there.
And then, uh, so yeah, it was kind of like a fun learning experience to kinda go into 'cause then I felt, like, more connected to the team.
So it actually helped my, like, onboarding as a full-time chief of staff, and it helped me, like, get to know the people.
It helped me kinda, like, fix a lot of systems and, like, go into overdrive into organizing everything too and, um, it made it easy to when we did f- Like, I knew how to find the right head of people when the time came and was able to onboard them successfully, which also, like, gave me a lot of pride in the role.
And I think being able to do all those things and having, you know, a CEO who, like, cares about the fact that you're doing all this and can respect it I think is also really helpful, and they can...
like, can see that kind of, um, your ability to kind of fill those gaps I think is the best way to show that you're leveling up.
And it was just, like, a fun experience too to just be like, "I accomplished this and was able to, like, help the company in a time of need." Great stories.
Um, I don't have a story, but this kind of, like, probed a question that I have that I, I've... Maybe you guys have been in similar situations, but how do you...
And it seems like you guys had teams that really supported your growth and the upel-upleveling. How... Have you been in a situation where you kinda had to show your value as a chief of staff?
Like, I've, uh, I was in the situation where they, they wanted a chief of staff. It was a startup, and so they're like, "Oh, this buzzword, we need this, I guess," right?
And so I joined, I'm like, "Yeah, I have all these ideas," but the CEO is still really apprehensive of like, "Well, how do I fit you in our org? I feel like we need you." And I was...
It was my ner- first role, so it was a little hard to kind of even, like, display that correctly to him.
So I don't know if you guys have any suggestions or ideas of what you've done or what you could do.I feel like I've had a lot of these type of bosses in the past, and, um, it definitely is, like, a really difficult barrier.
But I think one thing I've learned is sometimes if you just tell them you can do it, it's really not enough. Like, I've had a CEO in the middle of, like, raising a series was, uh, they had
three or four of the main executives quit. Well, one got let go, and the other two, the other ones quit. So it was kind of like, great, well, now you don't have anyone to put in your pitch deck.
So, like, let me see how I can like... [laughing] And I was like, "Well, here I can do...
This is, like, my expertise, but this is where I can kind of step in a little bit," and it's like, it's kind of like forcing your way in and being like, "Here's what I can make and do other than, like, make your pitch deck for you.
Like, I can actually, like, step in, and I'm good at presenting to board members and, um, have connections to VCs," or something like that.
Just, like, being able to, like, show, um, so I've definitely had to do that in more than one cases. And I've had cases where I've had a boss that did not appreciate that, and I like...
And you can't make your way through, and that's when situations where I've also felt like I had to leave.
'Cause I knew I was never gonna make any growth or do anything that I felt was, you know, maybe told to me at the beginning or felt that I was gonna be able to step into and was being blocked for whatever situation.
But it's definitely hard, but being able to showcase that and having your boss appreciate it is probably the best way to kind of get in. But it's, there's definitely a lot of barriers to kind of get to that point.
So a lot of it is dependent on your, on who you're working for. I wanna say something, and then I have a question for the group, and someone volunteer to answer, um, or everyone volunteer to answer.
Um, actually at my, uh, at my job, um, or just in i- in the past, I really should say, I've had some managers who have said, like, "You should try to prove breadth through depth."
So in the sense of like, it's, it's, it almost feels, I don't know, maybe this is a me thing, but sometimes it almost feels impossible to level up as a chief of staff because you're already doing everything.
How much more can you possibly do? But then again, there's like always more to do, but then you feel like I, I just, I feel like I'm already touching everything. Like what more can I do?
And so what I always say is like, I, I try to find a couple of areas where I can go a little bit deeper in to get some expertise, do really well in those things.
Obviously, you need to like support a lot of things as a chief of staff, but try to get really good at a few things.
Then you can prove value by becoming a little bit of an expert rather than generalist, and then people will continue to come to you for a lot of things. So it's almost like, it's, it's like
rather than go up, it's almost just like build this like vertical pole that you can like go up and down, and then you build the T shape from there.
Um, I have a question similarly above all, um, and sim- kind of what, what you were saying.
Like as a chief of staff, you're already working a ton of hours, uh, and you're already like the person that they call at eight o'clock at night when something is wrong, and you're almost just like, uh, you're, you're like prohibited from not dropping everything to fix it.
Um, and maybe that's a bold statement, but I'm curious when you think about trying to level up, like, and if that takes even more hours than you're already putting on, how do you find the balance of it all?
Like how do you keep yourself sane through such a high leverage, high powered, you know, high velocity, high everything role? Like how do you keep yourselves balanced and like stay true to yourself?
I can say something, um, just because I listen to a lot of podcasts, and I feel like some people might be scared of now becoming a chief of staff with everything that we're saying.
[laughing] It's great to be a chief of staff. Like yeah, it's a lot of work, but it's, uh, like people recognize it. I would say that it's very important to have a great attitude.
Of course, everyone has bosses and other bosses or like colleagues and other colleagues, so you just have to have like the right s- uh, mindset, right attitude.
But in terms of like level n- leveling up, to your point, I think that, um, yeah, it's important to, uh, become an expert on the field that you want to eventually specialize in, if that's what you want to do.
But I also feel like being a generalist is a great, like, value for the company 'cause you know everything that's going on, so you know what product is doing, what customer success, revenue, like basically everyone is doing.
So if they come up with questions, you know who to like direct them to, and I just feel like that's very valuable 'cause in the future, like I don't know, in your next role or if you continue in that company, you're able to bring a lot of value.
But yeah, for sure, uh, in my case, for example, I was chief of staff. I wanted to specialize in operations, so my, my boss was very understanding, and he wanted me to succeed, so now I'm doing more operations.
But I'm still like a generalist, and I, I really like that. I, I feel like I bring a lot of value by being a generalist. Anyone has... I'll go back to responding in terms of,
yeah, how, how are we balancing it all, and chief of staff is still a great job. Um, I think it answers if you are thinking about chief of staff too.
The generalist role was largely the arc of my career when I first started working across different departments.
But what I found, and I think it's true in most chief of staff roles, eventually through some project you're on, you become akin to one team, and you do start specializing there, and then that, depending on your timing of your role and what you are signing up for in terms of what they thought the chief of staff journey looks like.
In some companies, right, it's 12 months, 16 month.
There's a cycle to it that my belief is that your intention should be to specialize at some point when you do feel like it's your time is coming to an end in chief of staff, and you've found a good fit team, and then make that your transition.
So in my case-I started-- I'd always worked with commercial really closely, and then there just became the opportunity of where I was building pipeline with advisor and board networks and was outpacing our SDR business development team of nine people, and I enjoyed it.
I started to be more external facing, and then that became both my specialization and then my next step out of chief of staff. So.
The other piece too to balance is to figure out what your superpowers are and then figure out what your team's superpowers are and leverage them, whether it's through delegation, through partnership.
That's the way you scale, right? So for example, um, I was working with a leader within our group. She needed to redo her strategy for her campaign and was just getting stuck.
And I could have taken that on because I've done a lot of that work. But what I did was I gave her the tools. I gave her the templates.
I also sat down with her, helped her figure out what was blocking her, and then just worked side by side with her. That meant minimal number of hours on my end.
And then she could take that back and then create all of that with her team. Any, um, closing thoughts, final stories before we eat? I'm getting hungry.
I don't know if anyone else is hungry. [laughs] Um.
I guess just to kind of wrap up into like balancing and stuff, I guess one thing I tend to forget and I feel like is a good reminder for a lot of people is first like setting, also setting boundaries, um, very early, um, with your boss and then
take vacation. [laughs] Like take the time. Like I- If you can take vacation. Yeah, if you can. But I mean, I, I had a very, very...
I had like-- But when I was a executive assistant, when I started, I actually had like four or five bosses and it was rough.
Um, I worked like crazy, crazy hours just to like maintain everything, but I made a deal with them. I was like,
um, I was like, "Well, you know, I will work on vacation if I can take unlimited vacation and we'll like work remote." Before that was a thing. This was in like twenty seventeen. And I was-- So I made a deal with them.
I was like, "Have I ever not responded while I'm on vacation?" They're like, "No." Like, "Have I ever not like fixed something if needed?"
Like you just get so good at being a generalist sometimes if you're like, especially if you've been at your job for a while. This isn't something I'd recommend like the first year maybe, depending on your boss.
But, um, and this was like very strict, like private equity type of company. And so I was like, "Okay, well then can I please like take this time and I will make sure that nothing falls through the cracks?"
And, um, and it actually worked. And I got to-- And it was like the only thing that kept me sane for a while.
Um, and I think that's just like important to remember if you're trying to like first like hold those boundaries and then take time for yourself so that you feel like your best and you do your best work when you get back.
And it's a good reminder for me to do right now. So thought it would be nice to bring up. Love it. Thanks everyone. Woo!
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